Citation: Dong Daoqing, Sun Yuanyuan, Li Guanghui, Yang Huan, Wang Zuli, Xu Xinming. Recent Progress in the Functionalization of Quinoline N-Oxide[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4071-4086. doi: 10.6023/cjoc202004047 shu

Recent Progress in the Functionalization of Quinoline N-Oxide

a.
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
b.
College of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005

Corresponding author: Wang Zuli, wangzulichem@163.com
Received Date: 29 April 2020
Revised Date: 30 June 2020
Available Online: 15 July 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21772107) and the Key Research and Development Plan of Shandong Province (No. 2019GSF108017)the National Natural Science Foundation of China 21772107the Key Research and Development Plan of Shandong Province 2019GSF108017

Figures(67)

Owning to their low cost and readily available, quinoline N-oxides are widely used in organic synthesis. The functionalization reactions of C(2) and C(8) position of quinoline N-oxides and the reaction mechanisms of these reactions are summaried. It will be helpful for the reaction of quinoline N-oxide in the future.
- quinolone N-oxide,
- nitrogen compounds,
- functionalization,
- reaction mechanism
1. [1]
  Khan, Q. A.; Lu, J.; Hecht, S. M. J. Nat. Prod. 2009, 72, 438. doi: 10.1021/np8007232
2. [2]
  Michael, J. P. Nat. Prod. Rep. 2007, 24, 223. doi: 10.1039/b509528j
3. [3]
  Salahuddin, A.; Inam, A.; van Zyl, R. L.; Heslop, D. C.; Chen, C.-T.; Avecilla, F.; Agarwal, S. M.; Azam, A. Bioorg. Med. Chem. 2013, 21, 3080. doi: 10.1016/j.bmc.2013.03.052
4. [4]
  Chung, P.-Y.; Bian, Z.-X.; Pun, H.-Y.; Chan, D.; Chan, A. S.-C.; Chui, C.-H.; Tang, J. C.-O.; Lam, K.-H. Future Med. Chem. 2015, 7, 947. doi: 10.4155/fmc.15.34
5. [5]
  Liang, Q.; Zhang, Y.; Zeng, M.; Guan, L.; Xiao, Y.; Xiao, F. Toxicol. Res. 2018, 7, 521. doi: 10.1039/C8TX00029H
6. [6]
  (a) Dong, D. Q.; Gao, X.; Li, L. X.; Hao, S. H.; Wang, Z. L. Res. Chem. Intermed. 2018, 44, 7557.
  (b) Liu, Q.; Cai, D.; Qi, Y.; Le, X. Acta Chim. Sinica 2020, 78, 263(in Chinese).
  (刘启雁, 蔡戴宏, 戚永育, 乐学义, 化学学报, 2020, 78, 263.)
7. [7]
  Hao, S. H.; Li, L. X.; Dong, D. Q.; Wang, Z. L. Chin. J. Catal. 2017, 38, 1664. doi: 10.1016/S1872-2067(17)62901-2
8. [8]
  (a) Dong, D. Q.; Zhang, H.; Wang, Z. L. RSC Adv. 2017, 7, 3780.
  (b) Zhu, C.; Kou, L.; Bao, X. Chin. J. Chem. 2020, 38, 57.
  (c) Zhang, L.; Wu, B.; Zhou, Y.; Xia, J.; Zhou, S.; Wang, S. Chin. J. Chem. 2013, 31, 465.
9. [9]
  Zhang, L.; Wang, Y. Synthesis 2015, 47, 289. doi: 10.1055/s-0034-1379884
10. [10]
  Yan, G.; Borah, A. J.; Yang, M. Adv. Synth. Catal. 2014, 356, 2375. doi: 10.1002/adsc.201400203
11. [11]
  Yang, Y.; Guo, J.; Liu, Z. Chin. J. Org. Chem. 2019, 39, 1913(in Chinese).
12. [12]
13. [13]
  Dong, D.; Li, G.; Chen, D.; Sun, Y.; Han, Q.; Wang, Z.; Xu, X.; Yu, X. Chin. J. Org. Chem. 2020, 40, 1766(in Chinese).
14. [14]
  Dong, D. Q.; Hao, S. H.; Wang, Z. L. Mini-Rev. Org. Chem. 2017, 14, 130. doi: 10.2174/1570193X14666170207145101
15. [15]
  Dong, D. Q.; Chen, W. J.; Yang, Y.; Gao, X.; Wang, Z. L. ChemistrySelect 2019, 4, 2480. doi: 10.1002/slct.201900060
16. [16]
  Xie, L. Y.; Jiang, L. L.; Tan, J. X.; Wang, Y.; Xu, X. Q.; Zhang, B.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 14153. doi: 10.1021/acssuschemeng.9b02822
17. [17]
  Zhu, Z. F.; Zhang, M. M.; Liu, F. Org. Biomol. Chem. 2019, 17, 1531. doi: 10.1039/C8OB02786B
18. [18]
  Zhang, C.; Zhao, J. P.; Hu, B. W.; Shi, J.; Chen, D. Organometallics 2019, 38, 654. doi: 10.1021/acs.organomet.8b00847
19. [19]
  Yan, H.; Hou, Z. W.; Xu, H. C. Angew. Chem., Int. Ed. 2019, 58, 4592. doi: 10.1002/anie.201814488
20. [20]
  Hao, S. H.; Li, L. X.; Dong, D. Q.; Wang, Z. L.; Yu, X. Y. Tetrahedron Lett. 2018, 59, 4073. doi: 10.1016/j.tetlet.2018.10.001
21. [21]
  Wu, Z.; Pi, C.; Cui, X.; Bai, J.; Wu, Y. Adv. Synth. Catal. 2013, 355, 1971. doi: 10.1002/adsc.201300111
22. [22]
  Larionov, O. V.; Stephens, D.; Mfuh, A.; Chavez, G. Org. Lett. 2014, 16, 864. doi: 10.1021/ol403631k
23. [23]
  Kumar, R.; Kumar, I.; Sharma, R.; Sharma, U. Org. Biomol. Chem. 2016, 14, 2613. doi: 10.1039/C5OB02600H
24. [24]
  Yu, S.; Sang, H. L.; Ge, S. Angew. Chem., Int. Ed. 2017, 56, 15896. doi: 10.1002/anie.201709411
25. [25]
  Sen, C.; Ghosh, S. C. Adv. Synth. Catal. 2018, 360, 905. doi: 10.1002/adsc.201701330
26. [26]
  Yuan, J.-W.; Li, W.-J.; Xiao, Y.-M. Tetrahedron 2017, 73, 179. doi: 10.1016/j.tet.2016.11.070
27. [27]
  Yuan, J.-W.; Qu, L.-B. Chin. Chem. Lett. 2017, 28, 981. doi: 10.1016/j.cclet.2017.01.016
28. [28]
  Yuan, J.-W.; Liu, S.-N.; Qu, L.-B. Tetrahedron 2017, 73, 2267. doi: 10.1016/j.tet.2017.03.009
29. [29]
  Li, W.-Z.; Wang, Z.-X. Asian J. Org. Chem. 2018, 7, 2527. doi: 10.1002/ajoc.201800560
30. [30]
  Yuan, Y.; Jiang, M.; Wang, T.; Xiong, Y.; Li, J.; Guo, H.; Lei, A. Chem. Commun. 2019, 55, 11091. doi: 10.1039/C9CC05841A
31. [31]
  Liu, Q.; Wu, L.-Z. Natl. Sci. Rev. 2017, 4, 359. doi: 10.1093/nsr/nwx039
32. [32]
  Zhang, X.; Han, Y.; Lin, L.; Liu, Y. Chin. J. Org. Chem. 2019, 39 2705(in Chinese).
33. [33]
  Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China:Chem. 2019, 62, 24. doi: 10.1007/s11426-018-9399-2
34. [34]
  Gou, B.; Yang, C.; Zhang, L.; Xia, W. Acta Chim. Sinica 2017, 75, 66(in Chinese). doi: 10.11862/CJIC.2017.005
35. [35]
  Li, G.-H.; Han, Q.-Q.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Xu, X.-M.; Yu, X.-Y. Chin. Chem. Lett. 2020, 31, 3255. doi: 10.1016/j.cclet.2020.03.007
36. [36]
  Muhammad, M. H.; Chen, X.-L.; Liu, Y.; Shi, T.; Peng, Y.; Qu, L.; Yu, B. ACS Sustainable Chem. Eng. 2020, 8, 2682. doi: 10.1021/acssuschemeng.9b06010
37. [37]
  He, S.; Chen, X.; Zeng, F.; Lu, P.; Peng, Y.; Qu, L.; Yu, B. Chin. Chem. Lett. 2020, 31, 1863. doi: 10.1016/j.cclet.2019.12.031
38. [38]
  Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 2243. doi: 10.1021/acs.joc.8b02981
39. [39]
  Peng, S.; Lin, Y.; He, W. Chin. J. Org. Chem. 2020, 40, 541(in Chinese).
40. [40]
  Zhou, M.; Qin, P.; Jing, L.; Sun, J.; Du, H. Chin. J. Org. Chem. 2020, 40, 598(in Chinese).
41. [41]
  Li, Z.; Jin, J.; Huang, S. Chin. J. Org. Chem. 2020, 40, 563(in Chinese).
42. [42]
  Li, D.; Liang, C.; Jiang, Z.; Zhang, J.; Zhuo, W. T.; Zou, F. Y.; Wang, W. P.; Gao, G. L.; Song, J. J. Org. Chem. 2020, 85, 2733. doi: 10.1021/acs.joc.9b02933
43. [43]
  Wang, H.; Pei, Y.; Bai, J.; Zhang, J.; Wu, Y.; Cui, X. RSC Adv. 2014, 4, 26244. doi: 10.1039/C4RA02820A
44. [44]
  Chen, X.; Cui, X.; Yang, F.; Wu, Y. Org. Lett. 2015, 17, 1445. doi: 10.1021/acs.orglett.5b00330
45. [45]
  Kumar, R.; Kumar, R.; Dhiman, A. K.; Sharma, U. Asian J. Org. Chem. 2017, 6, 1043. doi: 10.1002/ajoc.201700267
46. [46]
  Bering, L.; Antonchick, A. P. Org. Lett. 2015, 17, 3134. doi: 10.1021/acs.orglett.5b01456
47. [47]
  Xu, F.; Li, Y.; Huang, X.; Fang, X.; Li, Z.; Jiang, H.; Qiao, J.; Chu, W.; Sun, Z. Adv. Synth. Catal. 2018, 361, 520.
48. [48]
  Sarmah, B. K.; Konwar, M.; Bhattacharyya, D.; Adhikari, P.; Das, A. Adv. Synth. Catal. 2019, 361, 5616. doi: 10.1002/adsc.201901103
49. [49]
  Xia, H.; Liu, Y.; Zhao, P.; Gou, S.; Wang, J. Org. Lett. 2016, 18, 1796. doi: 10.1021/acs.orglett.6b00522
50. [50]
  Zhang, Z.; Pi, C.; Tong, H.; Cui, X.; Wu, Y. Org. Lett. 2017, 19, 440. doi: 10.1021/acs.orglett.6b03399
51. [51]
  Wagh, S. B.; Singh, R. R.; Sahani, R. L.; Liu, R.-S. Org. Lett. 2019, 21, 2755. doi: 10.1021/acs.orglett.9b00705
52. [52]
  Chen, X.; Yang, F.; Cui, X.; Wu, Y. Adv. Synth. Catal. 2017, 359, 3922. doi: 10.1002/adsc.201700931
53. [53]
  Liang, C.; Zhuo, W.-T.; Niu, Y.-N.; Gao, G.-L. Synthesis 2020, 52, 219. doi: 10.1055/s-0039-1690726
54. [54]
  Li, G. H.; Dong, D. Q.; Yang, Y.; Yu, X. Y.; Wang, Z. L. Adv. Synth. Catal. 2019, 361, 832.
55. [55]
  Ye, S.; Qiu, G.; Wu, J. Chem. Commun. 2019, 55, 1013. doi: 10.1039/C8CC09250H
56. [56]
  Qiu, G.; Lai, L.; Cheng, J.; Wu, J. Chem. Commun. 2018, 54, 10405. doi: 10.1039/C8CC05847D
57. [57]
  Li, G. H.; Dong, D. Q.; Deng, Q.; Yan, S. Q.; Wang, Z. L. Synthesis-Stuttgart 2019, 51, 3313. doi: 10.1055/s-0037-1611787
58. [58]
  Dong, D. Q.; Li, L. X.; Li, G. H.; Deng, Q.; Wang, Z. L.; Long, S. Chin. J. Catal. 2019, 40, 1494. doi: 10.1016/S1872-2067(19)63420-0
59. [59]
  Wang, L.; Zhang, Y.; Zhang, M.; Bao, P.; Lv, X.; Liu, H.-G.; Zhao, X.; Li, J.-S.; Luo, Z.; Wei, W. Tetrahedron Lett. 2019, 60, 1845. doi: 10.1016/j.tetlet.2019.06.017
60. [60]
  Bao, P.; Wang, L.; Liu, Q.; Yang, D.; Wang, H.; Zhao, X.; Yue, H.; Wei, W. Tetrahedron Lett. 2019, 60, 214. doi: 10.1016/j.tetlet.2018.12.016
61. [61]
  Yang, D.; Sun, P.; Wei, W.; Liu, F.; Zhang, H.; Wang, H. Chem.-Eur. J. 2018, 24, 4423. doi: 10.1002/chem.201705866
62. [62]
  Li, G.; Gan, Z.; Kong, K.; Dou, X.; Yang, D. Adv. Synth. Catal. 2019, 361, 1808. doi: 10.1002/adsc.201900157
63. [63]
  Sun, K.; Chen, X. L.; Zhang, Y. L.; Li, K.; Huang, X. Q.; Peng, Y. Y.; Qu, L. B.; Yu, B. Chem. Commun. 2019, 55, 12615. doi: 10.1039/C9CC06924K
64. [64]
  Tian, L.; Wan, J.-P.; Sheng, S. ChemCatChem 2020, 12, 2533. doi: 10.1002/cctc.202000244
65. [65]
  Sun, K.; Chen, X. L.; Li, X.; Qu, L. B.; Bi, W. Z.; Chen, X.; Ma, H. L.; Zhang, S. T.; Han, B. W.; Zhao, Y. F.; Li, C. J. Chem. Commun. 2015, 51, 12111. doi: 10.1039/C5CC04484G
66. [66]
  Su, Y.; Zhou, X.; He, C.; Zhang, W.; Ling, X.; Xiao, X. J. Org. Chem. 2016, 81, 4981. doi: 10.1021/acs.joc.6b00475
67. [67]
  Wang, R.; Zeng, Z.; Chen, C.; Yi, N.; Jiang, J.; Cao, Z.; Deng, W.; Xiang, J. Org. Biomol. Chem. 2016, 14, 5317. doi: 10.1039/C6OB00925E
68. [68]
  Yu, H.; Pi, C.; Wang, Y.; Cui, X.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 124(in Chinese).
69. [69]
  Han, Q.-Q.; Li, G.-H.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Yu, X.-Y.; Xu, X.-M. Tetrahedron Lett. 2020, 61, 151704. doi: 10.1016/j.tetlet.2020.151704
70. [70]
  Dong, D. Q.; Chen, W. J.; Chen, D. M.; Li, L. X.; Li, G. H.; Wang, Z. L.; Deng, Q.; Long, S. Chin. J. Org. Chem. 2019, 39, 3190(in Chinese).
71. [71]
  Li, L. X.; Dong, D. Q.; Hao, S. H.; Wang, Z. L. Tetrahedron Lett. 2018, 59, 1517. doi: 10.1016/j.tetlet.2018.03.023
72. [72]
  Bao, P.; Wang, L.; Yue, H.; Shao, Y.; Wen, J.; Yang, D.; Zhao, X.; Wang, H.; Wei, W. J. Org. Chem. 2019, 84, 2976. doi: 10.1021/acs.joc.8b02844
73. [73]
  Huang, G.; Li, X.; Luo, J.; Luo, Z.; Tan, M. Chin. J. Org. Chem. 2019, 39, 617(in Chinese).
74. [74]
  Hui, R.; Zhang, S.; Tan, Z.; Wu, X.; Feng, B. Chin. J. Org. Chem. 2017, 37, 3060(in Chinese).
75. [75]
  Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2016, 18, 4144. doi: 10.1021/acs.orglett.6b02289
76. [76]
  Mai, W.; Lv, M.; Zhang, X.; Lu, K. J. Chem. Res. 2017, 41, 705. doi: 10.3184/174751917X15125690124246
77. [77]
  Li, P.; Jiang, Y.; Li, H.; Dong, W.; Peng, Z.; An, D. Synth. Commun. 2018, 48, 1909. doi: 10.1080/00397911.2018.1460670
78. [78]
  Sumunnee, L.; Buathongjan, C.; Pimpasri, C.; Yotphan, S. Eur. J. Org. Chem. 2017, 2017, 1025. doi: 10.1002/ejoc.201601443
79. [79]
  Fu, W.-K.; Sun, K.; Qu, C.; Chen, X.-L.; Qu, L.-B.; Bi, W.-Z.; Zhao, Y.-F. Asian J. Org. Chem. 2017, 6, 492. doi: 10.1002/ajoc.201700001
80. [80]
  Xie, L.-Y.; Peng, S.; Liu, F.; Chen, G.-R.; Xia, W.; Yu, X.; Li, W.-F.; Cao, Z.; He, W.-M. Org. Chem. Front. 2018, 5, 2604. doi: 10.1039/C8QO00661J
81. [81]
  Peng, S.; Song, Y.-X.; He, J.-Y.; Tang, S.-S.; Tan, J.-X.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2287. doi: 10.1016/j.cclet.2019.08.002
82. [82]
  Jiang, M.; Yuan, Y.; Wang, T.; Xiong, Y.; Li, J.; Guo, H.; Lei, A. Chem. Commun. 2019, 55, 13852. doi: 10.1039/C9CC07777D
83. [83]
  You, G.; Xi, D.; Sun, J.; Hao, L.; Xia, C. Org. Biomol. Chem. 2019, 17, 9479. doi: 10.1039/C9OB02106J
84. [84]
  Cai, H.; Yang, H.; Xu, J.; Bao, H.; Huang, L.; Zhang, H.; Zhang, P.; Li, W. Asian J. Org. Chem. 2019, 8, 2105. doi: 10.1002/ajoc.201900548
85. [85]
  Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M. Green Chem. 2019, 21, 3858. doi: 10.1039/C9GC01175G
86. [86]
  Xie, L.-Y.; Li, Y.-J.; Qu, J.; Duan, Y.; Hu, J.; Liu, K.-J.; Cao, Z.; He, W.-M. Green Chem. 2017, 19, 5642. doi: 10.1039/C7GC02304A
87. [87]
  Lai, M.; Zhai, K.; Cheng, C.; Wu, Z.; Zhao, M. Org. Chem. Front. 2018, 5, 2986. doi: 10.1039/C8QO00840J
88. [88]
  Zhang, S.-B.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2019, 227, 109367. doi: 10.1016/j.jfluchem.2019.109367
89. [89]
  Li, G.; Jia, C.; Sun, K. Org. Lett. 2013, 15, 5198. doi: 10.1021/ol402324v
90. [90]
  Xie, L. Y.; Peng, S.; Liu, F.; Yi, J. Y.; Wang, M.; Tang, Z.; Xu, X.; He, W. M. Adv. Synth. Catal. 2018, 360, 4259. doi: 10.1002/adsc.201800918
91. [91]
  Chen, X.; Peng, M.; Huang, H.; Zheng, Y.; Tao, X.; He, C.; Xiao, Y. Org. Biomol. Chem. 2018, 16, 6202. doi: 10.1039/C8OB00862K
92. [92]
  Xie, L.-Y.; Peng, S.; Lu, L.-H.; Hu, J.; Bao, W.-H.; Zeng, F.; Tang, Z.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 7989. doi: 10.1021/acssuschemeng.8b01358
93. [93]
  Xie, L.-Y.; Peng, S.; Liu, F.; Liu, Y.-F.; Sun, M.; Tang, Z.-L.; Jiang, S.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 7193. doi: 10.1021/acssuschemeng.9b00200
94. [94]
  Yu, H.; Dannenberg, C. A.; Li, Z.; Bolm, C. Chem.-Asian J. 2016, 11, 54. doi: 10.1002/asia.201500875
95. [95]
  Yu, X.; Yang, S.; Zhang, Y.; Guo, M.; Yamamoto, Y.; Bao, M. Org. Lett. 2017, 19, 6088. doi: 10.1021/acs.orglett.7b02922
96. [96]
  Han, S.; Gao, X.; Wu, Q.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Org. Chem. Front. 2019, 6, 830. doi: 10.1039/C8QO01281D
97. [97]
  Zhu, C.; Yi, M.; Wei, D.; Chen, X.; Wu, Y.; Cui, X. Org. Lett. 2014, 16, 1840. doi: 10.1021/ol500183w
98. [98]
  Li, G.; Jia, C.; Sun, K.; Lv, Y.; Zhao, F.; Zhou, K.; Wu, H. Org Biomol. Chem. 2015, 13, 3207. doi: 10.1039/C5OB00135H
99. [99]
  Wang, Z.; Han, M.-Y.; Li, P.; Wang, L. Eur. J. Org. Chem. 2018, 2018, 5954. doi: 10.1002/ejoc.201800963
100. [100]
  Behera, A.; Sau, P.; Sahoo, A. K.; Patel, B. K. J. Org. Chem. 2018, 83, 11218. doi: 10.1021/acs.joc.8b01797
101. [101]
  Xie, L.-Y.; Peng, S.; Jiang, L.-L.; Peng, X.; Xia, W.; Yu, X.; Wang, X.-X.; Cao, Z.; He, W.-M. Org. Chem. Front. 2019, 6, 167. doi: 10.1039/C8QO01128A
102. [102]
  Kim, D.; Ghosh, P.; Kwon, N. Y.; Han, S. H.; Han, S.; Mishra, N. K.; Kim, S.; Kim, I. S. J. Org. Chem. 2020, 85, 2476. doi: 10.1021/acs.joc.9b03173
103. [103]
  Chen, X.; Li, X.; Qu, Z.; Ke, D.; Qu, L.; Duan, L.; Mai, W.; Yuan, J.; Chen, J.; Zhao, Y. Adv. Synth. Catal. 2014, 356, 1979. doi: 10.1002/adsc.201301065
104. [104]
  Bi, W.-Z.; Sun, K.; Qu, C.; Chen, X.-L.; Qu, L.-B.; Zhu, S.-H.; Li, X.; Wu, H.-T.; Duan, L.-K.; Zhao, Y.-F. Org. Chem. Front. 2017, 4, 1595. doi: 10.1039/C7QO00311K
105. [105]
  Li, P.; Zhao, J.; Xia, C.; Li, F. Org. Chem. Front. 2015, 2, 1313. doi: 10.1039/C5QO00204D
106. [106]
  Chen, X.; Zhu, C.; Cui, X.; Wu, Y. Chem. Commun. 2013, 49, 6900. doi: 10.1039/c3cc43947j
107. [107]
  Bi, W.-Z.; Qu, C.; Chen, X.-L.; Qu, L.-B.; Liu, Z.-D.; Sun, K.; Li, X.; Zhao, Y.-F. Eur. J. Org. Chem. 2017, 2017, 5125. doi: 10.1002/ejoc.201701080
108. [108]
  Zhang, D.; Qiao, K.; Hua, J.; Liu, Z.; Qi, H.; Yang, Z.; Zhu, N.; Fang, Z.; Guo, K. Org. Chem. Front. 2018, 5, 2340. doi: 10.1039/C8QO00499D
109. [109]
  Wang, D.; Jia, H.; Wang, W.; Wang, Z. Tetrahedron Lett. 2014, 55, 7130. doi: 10.1016/j.tetlet.2014.11.005
110. [110]
  Stephens, D. E.; Lakey-Beitia, J.; Atesin, A. C.; Ateşin, T. A.; Chavez, G.; Arman, H. D.; Larionov, O. V. ACS Catal. 2015, 5, 167. doi: 10.1021/cs501813v
111. [111]
  Stephens, D. E.; Lakey-Beitia, J.; Chavez, G.; Ilie, C.; Arman, H. D.; Larionov, O. V. Chem. Commun. 2015, 51, 9507. doi: 10.1039/C5CC02227D
112. [112]
  Chen, X.; Cui, X.; Wu, Y. Org. Lett. 2016, 18, 2411. doi: 10.1021/acs.orglett.6b00923
113. [113]
  Chen, X.; Cui, X.; Wu, Y. Org. Lett. 2016, 18, 3722. doi: 10.1021/acs.orglett.6b01746
114. [114]
  Li, G. H.; Dong, D. Q.; Yu, X. Y.; Wang, Z. L. New J. Chem. 2019, 43, 1667. doi: 10.1039/C8NJ05374J
115. [115]
  Zhang, X.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2014, 53, 10794. doi: 10.1002/anie.201406747
116. [116]
  Sharma, U.; Park, Y.; Chang, S. J. Org. Chem. 2014, 79, 9899. doi: 10.1021/jo501995c
117. [117]
  You, C.; Pi, C.; Wu, Y.; Cui, X. Adv. Synth. Catal. 2018, 360, 4068. doi: 10.1002/adsc.201800659
118. [118]
  Wang, B.; Li, C.; Liu, H. Adv. Synth. Catal. 2017, 359, 3029. doi: 10.1002/adsc.201700484
119. [119]
  Shibata, T.; Matsuo, Y. Adv. Synth. Catal. 2014, 356, 1516. doi: 10.1002/adsc.201400223
120. [120]
  Sharma, R.; Kumar, R.; Kumar, I.; Sharma, U. Eur. J. Org. Chem. 2015, 2015, 7519. doi: 10.1002/ejoc.201501246
121. [121]
  Li, J.; Wang, H.; Hou, Y.; Yu, W.; Xu, S.; Zhang, Y. Eur. J. Org. Chem. 2016, 2016, 2388. doi: 10.1002/ejoc.201600332
122. [122]
  You, C.; Yuan, T.; Huang, Y.; Pi, C.; Wu, Y.; Cui, X. Org. Biomol. Chem. 2018, 16, 4728. doi: 10.1039/C8OB01108G
1. [1]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
2. [2]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
3. [3]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
4. [4]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
5. [5]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
6. [6]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
7. [7]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
8. [8]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
9. [9]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
10. [10]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
11. [11]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
12. [12]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
13. [13]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
14. [14]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
15. [15]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
16. [16]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
17. [17]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
18. [18]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
19. [19]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
20. [20]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

Get Citation

PDF

XML

Metrics

PDF Downloads(160)
Abstract views(5435)
HTML views(1137)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142